Tetrahydrofuran → 5-(Pyrrolidin-1-ylsulfonyl)indoline-2,3-dione

HRID 853873Notes

Reaction equation

HRID 853873 reaction equation
[O:1]=[C:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12](Cl)(=[O:14])=[O:13])[CH:8]=2)[NH:3]1.C1COCC1.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.C(N(CC)C(C)C)(C)C>C(Cl)(Cl)Cl>[N:21]1([S:12]([C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[NH:3][C:2](=[O:1])[C:10]3=[O:11])(=[O:14])=[O:13])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 159089472,3-Dioxoindoline-5-sulfonyl chloride

Product 1

HCID 41173815-(Pyrrolidin-1-ylsulfonyl)indoline-2,3-dioneYield 39%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a cold solution of 2,3-dioxo-2,3-dihydro-1H-indole-5-sulfonylchloride (2.00 g, 8.14 mmol) in a 1:1 mixture of THF: CHCl3 (96 mL) was added drop-wise via syringe pump over a period of 1 hr a solution of pyrrolidine (0.885 mL, 10.6 mmol) and N,N-diisopropylethyl amine (2.84 mL, 16.3 mmol, 2 eq) in chloroform (16 mL) under a dry N2 atmosphere with cooling in an ice bath. After stirring for 1 h., the reaction was concentrated. The crude product was purified on Biotage KP silica gel eluting with 80/20 CH2Cl2/EtOAc to give the title compound as a greenish-yellow solid (0.88 g, 39% yield). NMR (300 Mz, DMSO-d6): consistent. MS: (ES−) m/z 279 [M−H].

Workup

  1. temperaturewith cooling in an ice bath
  2. concentrationthe reaction was concentrated
  3. customThe crude product was purified on Biotage KP silica gel eluting with 80/20 CH2Cl2/EtOAc

Sources & evidence

ORD record
ord-88af5cfee3aa4f6e95e7a4663bcc945e
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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